1,3-Cyclohexanedione → 3-Oxo-1-cyclohexenyl 2,4-dibromo-3-(2-ethoxyiminopropyloxy)-benzoate

HRID 585330Notes

Reaction equation

HRID 585330 reaction equation
[Br:1][C:2]1[C:10]([O:11][CH2:12][C:13](=[N:15][O:16][CH2:17][CH3:18])[CH3:14])=[C:9]([Br:19])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[C:20]1(=O)[CH2:25][CH2:24][CH2:23][C:22](=[O:26])[CH2:21]1.Cl.CN(C)CCCN=C=NCC.CN(C1C=CC=CN=1)C>C(Cl)Cl>[Br:1][C:2]1[C:10]([O:11][CH2:12][C:13](=[N:15][O:16][CH2:17][CH3:18])[CH3:14])=[C:9]([Br:19])[CH:8]=[CH:7][C:3]=1[C:4]([O:6][C:20]1[CH2:25][CH2:24][CH2:23][C:22](=[O:26])[CH:21]=1)=[O:5]

Participants

6

Reactant 4

HCID 104341,3-CyclohexanedioneHCID 218852-DimethylaminopyridineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 858737862,4-Dibromo-3-(2-ethoxyiminopropyloxy)benzoic acid

Product 1

HCID 865945983-Oxo-1-cyclohexenyl 2,4-dibromo-3-(2-ethoxyiminopropyloxy)-benzoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

0.280 g (0.70 mmol) of 2,4-dibromo-3-(2-ethoxyiminopropyloxy)benzoic acid, 0.087 g (0.80 mmol) of cyclohexane-1,3-dione, 0.139 g (0.70 mmol) of N′-(3-dimethylaminopropyl)-N-ethylcarbodiimide hydrochloride and 0.001 g of dimethylaminopyridine were stirred in 15 ml of CH2Cl2 at RT for 3 h. The mixture was then diluted with CH2Cl2 and washed with 0.5 N HCl, water, saturated NaHCO3 solution and again with water. The combined organic phases were dried over Na2SO4 and evaporated to dryness, giving 3-oxo-1-cyclohexenyl 2,4-dibromo-3-(2-ethoxyiminopropyloxy)-benzoate in the form of a yellow resin of sufficient purity.

Workup

  1. washwashed with 0.5 N HCl, water, saturated NaHCO3 solution and again with water
  2. dry with materialThe combined organic phases were dried over Na2SO4
  3. customevaporated to dryness

Sources & evidence

ORD record
ord-0612652a14fe4ac9bc60cb9f721be024
Source dataset
uspto-grants-2005_08
Patent number
US06930208B2

Reaction notes

Loading…